Evaporation of streams of liquid droplets in environments at vacuum pressures below the vapor pressure has not been widely studied. Here, experiments and simulations are reported that quantify the change in droplet diameter when a steady stream of ≈100 μm diameter drops is injected into a chamber initially evacuated to <10^{-8}bar. In experiments, droplets fall through the center of a 0.8 m long liquid nitrogen cooled shroud, simulating infinity radiation and vapor mass flux boundary conditions. Experimentally measured changes in drop diameters vary from ≈0 to 6 μm when the initial vapor pressure is increased from 10^{-6} to 10^{-3} bar by heating the liquid. Measured diameter changes are predicted by a model based on the Hertz-Knudsen equation. One uncertainty in the calculation is the "sticking coefficient" β. Assuming a constant β for all conditions studied here, predicted diameter changes best match measurements with β≈0.3. This value falls within the range of β reported in the literature for organic liquids. Finally, at the higher vapor pressure conditions considered here, the drop stream disperses transverse to the main flow direction. This spread is attributed to forces imparted by an absolute pressure gradient produced by the evaporating stream.